214472-41-0

Basic information

• Product Name: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester
• Synonyms: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester;Methyl 2-aMino-4-Methoxy-3-(3-Morpholinopropoxy)benzoate;Methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate;Methyl 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzoate
• CAS NO: 214472-41-0
• Molecular Formula: C₁₆H₂₄N₂O₅
• Molecular Weight: 324.37216
• Mol File: 214472-41-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester(214472-41-0)
• EPA Substance Registry System: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester(214472-41-0)

Safety Data

• Hazardous Substances Data: 214472-41-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzoic acid, 2-amino-4-methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester is utilized as an active pharmaceutical ingredient for the development of drugs targeting a range of diseases. Its unique structure and pharmacological activities make it a promising candidate for the treatment of conditions such as cancer and neurodegenerative disorders.
Used in Research Applications:
In the field of research, Benzoic acid, 2-amino-4-methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester serves as a reference standard for analytical testing. Its well-defined chemical structure and properties allow researchers to accurately measure and compare its activity against various biological targets, aiding in the discovery and optimization of new therapeutic agents.
Used in Drug Development:
Benzoic acid, 2-amino-4-methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester is employed as a lead compound in drug development. Its potential therapeutic effects and unique chemical structure make it a valuable starting point for the design and synthesis of new drugs with improved efficacy and safety profiles.
Used in Medicinal Chemistry:
In medicinal chemistry, Benzoic acid, 2-amino-4-methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester is used as a building block for the synthesis of novel compounds with potential therapeutic applications. Its versatile structure allows for the introduction of various functional groups and modifications, enabling the exploration of structure-activity relationships and the optimization of drug candidates.
Overall, Benzoic acid, 2-amino-4-methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester is a versatile and promising chemical compound with a wide range of applications in the pharmaceutical industry, research, and drug development. Its unique structure and pharmacological properties make it an invaluable asset in the ongoing quest for new and effective treatments for various diseases.

Upstream product

• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 215659-03-3 methyl 5-hydroxy-4-methoxy-2-nitrobenzoate 
• 645-08-9 Isovanillic acid 
• 380844-24-6 methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate 
• 380844-22-4 methyl 3-(3-chloropropoxy)-4-methoxybenzoate 
• 214472-17-0 4-methoxy-5-[3-(4-morpholinyl)propoxy]benzoic acid methyl ester 
• 214472-37-4 4-methoxy-5-(3-morpholinylpropoxy)-2-nitrobenzoic acid methyl ester 

Downstream Products

• 184475-35-2 gefitinib 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 
• 214486-62-1 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-7-methoxy-6-(3-morpholin-4-yl)-propoxyl-quinoline-3-carbonitrile 
• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 252264-46-3 ethyl 2-(dimethylaminomethyleneamino)-4-methoxy-5-(3-morpholin-4-yl-propoxy)benzoate 

Relevant articles and documents

Electroreduction preparation method of gefitinib intermediate

The invention discloses an electroreduction preparation method of a gefitinib intermediate. The electroreduction preparation method comprises the steps that an acidic aqueous solution of 4-methoxy-5-(3-morpholinylpropoxy)-2-nitrobenzoate is used as cathode liquor in a diaphragm electrolyzer; the acidic aqueous solution is used as anode liquor; and relative to a reference electrode, the voltage ofa cathode working electrode is 1.00V-2.50V, the current density of the cathode working electrode is 25.0 mA/cm-250.0 mA/cm, the working temperature of an electrolytic cell is between 25 DEG C-80DEG C, electrolysis is performed, and gefitinib intermediate 2-amino-4-methoxy-5-(3-morpholinylpropoxy)methyl benzoate is prepared. In the electroreduction process, a reducing agent or an organic solvent is not used, by changing the electrode potential, the conversion rate and selectivity can be controlled, and a high-purity and high-yield intermediate is obtained.

Anti-cancer drug gefitinib and analog intermediate electro-reduction preparation method thereof

The invention relates to an electroreduction preparation method of a 2-amino-4-methoxybenzoic acid derivative represented by a formula I, wherein the preparation reaction is defined in the specification, n is selected from 1, 2 and 3, X is selected from C

A new heterocyclic compound initiates ROS accumulation and cause apoptotic cell death in human bone cancer cells

A new heterocyclic compound 7-methoxy-6-(3-morpholinopropoxy)quinazolin-4(3H)-one (1), designed using methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (2) as the starting material, was successfully obtained via multiple synthesis route and finally characterized by fourier transform infrared (FT-IR) spectroscopy, 1H nuclear magnetic resonance (NMR), and single crystal X-ray crystallography. We investigated its effect on cell viability and proliferation with Cell Counting Kit-8 (CCK8) assay. The results revealed that compound 1 could block the proliferation of Saos-2 bone cancer cells. In addition, Annexin V-FITC/PI assay and Western blot analysis were performed to detect whether compound 1 could induce cell apoptosis. The results indicated that compound 1 could increase the number of apoptotic cells remarkably. Moreover, we examined the impact of compound 1 on ROS generation. Results revealed that compound 1 up-regulated the reactive oxygen species (ROS) genes expression and promoted the accumulation of ROS in Saos-2 cells. Finally, molecular docking has been utilized to study the binding mode of compound 1 with tubulin.

Method of Synthesizing 6,7-Substituted 4-Anilino Quinazoline

A method of synthesizing 6,7-substituted 4-anilino quinazoline employs 3,4-substituted benzoic acid as an initial reactant, and the 6,7-substituted 4-anilino quinazoline is obtained by an esterifying step, a nitrating step, a reducing step, a cyclizing step, and an one-pot reaction. In the above method, the initial reactant has low cost and yield. of the 6,7-substituted 4-anilino quinazoline is high, therefore, production cost can be reduced effectively, and competitive power of the product of the 6,7-substituted 4-anilino quinazoline can be improved.

A PROCESS FOR THE PREPARATION OF GEFITINIB

The present invention provides an improved, industrial advantageous process for the preparation of gefitinib of formula (I), and its pharmaceutically acceptable salts thereof in high yield and purity.

Novel preparation of gefitinib

A new synthesis of the anticancer drug gefitinib is described starting from methyl 3-hydroxy-4-methoxybenzoate.The sequence involves alkylation of the starting material, followed by nitration, reduction, cyclisation, chlorination and amination reactions.

Fluorine-18 labeling of 6,7-disubstituted anilinoquinazoline derivatives for positron emission tomography (PET) imaging of tyrosine kinase receptors: Synthesis of18F-Iressa and related molecular probes

Inhibitors of tyrosine kinase enzymatic activity represent a promising new class of antineoplastic agents. Although clinical studies performed over the last decade give more insight on the potential therapeutic applications of such drugs, identification of the individual patients who might benefit from them remains a major challenge. We have developed a synthetic strategy for the production of a wide variety of radiolabeled 6,7-disubstituted 4-anilinoquinazolines suitable for noninvasive imaging of tyrosine kinase receptors to predict therapy effectiveness. Three new F-18 labeled radiopharmaceuticals based on the therapeutic agents Tarceva, Iressa, and ZD6474 were synthesized. Decay-corrected yields varied between 25 and 40% for a total synthesis time of 120 min, thus providing F-18 labeled tyrosine kinase inhibitors in quantities and times practical for use as PET radiopharmaceuticals. Copyright

SUBSTITUTED 3-CYANO QUINOLINES

This invention provides compounds having formula (1), wherein: X is cycloalkyl which may be optionally substituted; or is a pyridinyl, pyrimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally substituted; n is 0-1; Y is -NH-, -O-, -S-, or -NR-; R is alkyl of 1-6 carbon atoms; R1, R2, R3 and R4 are each, independently, hydrogen, halogen, alkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, hydroxymethyl, halomethyl, alkanoyloxy, alkenoyloxy, alkynoyloxy, alkanoyloxymethyl, alkenoyloxymethyl, alkynoyloxymethyl, alkoxymethyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulfonamido, alkenylsulfonamido, alkynylsulfonamido, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy, carboalkyl, phenoxy, phenyl, thiophenoxy, benzyl, amino, hydroxyamino, alkoxyamino, alkylamino, dialkylamino, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, phenylamino, benzylamino, formulae (a, b, c, d, e, f, g, h, i, j, k, l, m, n, o, p, q or r); R5 is alkyl which may be optionally substituted, or phenyl which may be optionally substituted; R6 is hydrogen, alkyl, or alkenyl; R7 is chloro or bromo; R8 is hydrogen, alkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, N-cycloalkylaminoalkyl, N-cycloalkyl-N-alkylaminoalkyl, N,N-dicycloalkylaminoalkyl, morpholino-N-alkyl, piperidino-N-alkyl, N-alkyl-piperidino-N-alkyl, azacycloalkyl-N-alkyl, hydroxyalkyl, alkoxyalkyl, carboxy, carboalkoxy, phenyl, carboalkyl +, chloro, fluoro, or bromo; Z is amino, hydroxy, alkoxy, alkylamino, dialkylamino, morpholino, piperazino, N-alkylpiperazino, or pyrrolidino; m = 1-4, q = 1-3, and p = 0-3; any of the substituents R1, R2, R3 or R4 that are located on contiguous carbon atoms can together be the divalent radical -O-C(R8)2-O-; or a pharmaceutically acceptable salt thereof with the proviso that when Y is -NH-, R1, R2, R3 and R4 are hydrogen, and n is O, X is not 2-methylphenyl, which are inhibitors of protein tyrosine kinase.

Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: Analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents

The syntheses and biological evaluations of 4-anilinoquinoline-3-carbonitrile analogues of the three clinical lead 4-anilinoquinazolines Iressa, Tarceva, and CI-1033 are described. The EGFR and HER-2 kinase inhibitory activities and the cell growth inhibition of the two series are compared with each other and with the clinical lead EKB-569. Similar activities are observed between these two series.